He is able to categorize transactions, reconcile accounts, send out owner statements, pay vendors, p&l reporting, and other bookkeeping tasks.

After giving the past tenant time to pay the bill the property management company then sent the tenant to collections without consulting me. 

Most of these properties are fixed & flipped above market worth, and the bid side is sliding as you're paying over market.

Would the goal after I get a duplex to use the income streams and my work income to pay it off as soon as possible?

This is usually based on the proportion of the down payment, mortgage payments, and other costs each party contributes.Financing Details: Define who will pay for what.

I am also not adept to design, and pay a designer especially in today's competitive market. 

STR's require immaculate staging, marketing, and appeal to younger, high-earning audiences who will happily pay $300-500 / night for a "unique experience".

On the other hand, if I do go through insurance, they might find reasons not to pay out, resulting in another zero-dollar claim.Do you have any recommendations for where to find a reliable, trustworthy, transparent, and accurate insurance company or agent?

Our housing expense saved is $1,359 or $16,308 per yearThis makes our Total Net-worth ROI (NROI) much higher.NROI= ($9,556+$16,308)                   $75kNROI= ~34.4%These numbers will only get better if/when we are able to refinance to a lower rate and more principle pay down.Any other successful house hackers out there?

Its hard for investors to find good reliable contractors because typically investors want to pay below market prices for the work.